Systems and processes are provided for projecting, tracking and assessing the performance of and relative interests of the parties to one or more cooperatively-funded insurance policies, such as split-dollar or jointly-owned life insurance policies. Certain embodiments can also optimize the structure and function of existing insurance policies. Input data regarding actual and potential parties to an insurance contract, regulatory considerations, as well as the objectives that the parties intend to achieve, is used to propose, create, track, maintain, and implement an insurance policy or a group insurance plan. The input data is communicated to an enterprise platform via a web server. The enterprise platform includes applications which process the data. Data processing functions performed include proposal and policy generation, policy reevaluation and re-proposal, policy conversion, and report generation. The systems and processes optimize achievement of policy objectives and minimize tax consequences under applicable tax codes.